Evil Never Loved You
by FairyTale87
Summary: AU S3/S4. Sam leaves to pursue the powers Yellow-Eyes gave him, leaving Dean to continue hunting. Ruby then shows up, oddly wanting to help Dean. Their first hunt is in Mystic Falls, when they get word a vampire is in town... Dean/Ruby Dean/Katherine
1. Back on the Road Again

_Evil Never Loved You_

_One _

_Back on the Road Again _

The Daisy Inn motel could hardly even be considered suitable for inhabitance; it was so aged and frayed, that it was feared to collapse on itself at any minute. Plopped down in the corner of a town long since forgotten, somewhere in the depths of Minnesota, the melting snow took its toll on the already weak building. But for the Winchesters, the place was like a palace. The Daisy Inn was the best motel they had stayed at in months, and the slightly scratchy sheets could have very well been silk. Dean often wondered if it was a good or bad thing that a dump like Daily Inn could feel so much like—home. He wanted to believe it just showed their strength of character and adaptability, but he knew that was nowhere near the truth. The Daisy felt like home, because in all honesty, it was. John Winchester had raised his boys into a life where it didn't matter where you were, or how uncomfortable you were; all that mattered was the destination. Sam had habitually described himself and Dean as soldiers in their father's pointless army, but Dean begged to differ; he almost pleaded. If what they were doing was considered "nothing", and their hunting "unnecessary", then Dean would have such a bitterness towards his father, it would ultimately burst him into smithereens of dying and dead hopes.

But all of that traditional turmoil seemed superfluous in their current situation. Sam was about to walk out; for good this time. Dean could see it in his brother's stormy blue eyes: he wasn't kidding about this. Dean was shredding into a million fragile pieces of disjointed emotion, and had no power but to watch them surround him like a fortress of his own self loathing. If only he had kept Sammy safer; if only he had been more of a big brother, and less of a replica of dad; if only…

"Don't you have anything to say to me?" Sam asked harshly, jerking Dean from his thoughts. The elder Winchester looked up to his brother, searching for any of the old Sammy he once knew. It was lost somehow, in the abyss created by the fate Sam was now sure to have. The second power was introduced to Sam Winchester; Dean knew it was all over. Even if he had tried to deny it, he still knew. Sam was weak when it came to the temptation of control, and the damn yellow-eyed demon had placed that right in his hands.

"What's there to say," Dean drawled numbly, "if you're leaving, you're leaving; if you're not, you're not." He supplied Sam with a slight shrug of the shoulders, and returned his eyes to the brown bottle of beer sitting on the table beside him. It called to him in a melancholy hymn, just _craving_ to drown Dean's troubles in its intoxicating consistency.

"God, Dean, your self-pity is really getting old, you know that?" Sam's voice was a bitter heap of every insult he'd never gotten the chance to spew at his father. He had always hated his brother for continuing the ways of John, and wanted nothing more than to crush the idol Dean had created for himself, and in turn, him.

"The door's right there, Sammy," Dean muttered lowly in reply, not bothering to lift his eyes to his brother's seething features. Maybe it was wrong to just let him go; if this had been a year or so ago, Dean would be tying Sam down to keep him from leaving. But what did it matter now? Sam had more of a love for the dark powers he was now "blessed" with, and was willing to leave Dean in the dust when a better opportunity presented itself. Why the hell would Dean want to save _that_?

It was a lie, though. Dean Winchester would do anything for his brother, even if he became Satan himself. But it was too late to start down that road again. The last time that'd happened, he condemned himself to hell.

"You're impossible," Sam said darkly, and grabbed his bag off of the bed with a certain force Dean had never seen in him before. He knew Sammy, deep down, really didn't want to leave, but the temptation was too damn appealing for him not to. Maybe he wanted to watch Dean suffer; watch him fight to make him stay. But Dean wasn't about to give into those insidious wishes of Sam, and rather tried to stay as aloof as his heart could let him.

Watching as Sam breathed in heavily, Dean turned his back on him, again returning his gaze to the bottle of beer, and closed his eyes. They burned at the sensation of being rehydrated after a night of an hours sleep tops, but Dean refused to open them until he heard Sam slam the door shut.

He was gone.

Where he was off to, Dean hadn't a clue. Reaching into his pocket, he felt the cool metal of his keys, and couldn't help but smile sadly. He knew Sam wouldn't take the car anyways; it was too much of dad, too much of the past. It still tortured Dean though. The Impala was safe and sound, with all of the love and devotion it could possibly want, and Sam, his own flesh and blood, was now chained to the road, lost, and overall, dangerous. What kind of brother would allow his younger sibling to have that kind of life? Apparently Dean.

He was tired of saving Sam, especially when he didn't want to be saved. He was done with trying to make him accept the past, and he was certainly over with telling Sammy that everything would be alright.

They were better off going their separate ways; they had to be.

Moving his limp body slowly to the bed, bottle in hand, he sat down with a certain dead weight. Sam was gone, and he was alone. Dean had never done well being by himself. Of course he could get by, but it was not his true nature. He was a man of loyalty; he was a soldier, willing to give his life to save that of another. But now, who was there to fight for? Sammy had left, John was dead.

Rubbing a clammy hand over his face, it all didn't seem to matter. He'd go through the motions; drive the Impala around the country, saving people from monsters they didn't even know existed, and eat meals alone at a broke down motel in Nowheresville. Oh, what a _wonderful_ life.

* * *

><p>Whether it was morning or not could not be answered by the dark sky, but the obsessive knocking on the motel door could not be ignored. Dean groaned, rising his aching body off of the bed, and staggered his way to the door. Whipping it open with what little strength he had, he quietly prayed that it was Sam. Alas.<p>

"Ruby," Dean deadpanned in a husky, still partly asleep voice, "what an unpleasant surprise." He blockaded the entrance to the room with his perfectly chiseled body, and stared at Ruby in dark numbness.

"Your humor gets really cliché when you're tired," she stated in return, not bothering to shove Dean out of the way. She rather crossed her arms, feeling her blonde hair flutter in the wind. It almost gave her the illusion that she was human.

"Oh, so you're saying I'm funny, huh?" Dean smirked. What the hell was he doing? This was _Ruby_ he was talking to…

"That _is_ what I just said, wasn't it? God, am I speaking Greek or something?" She raked a hand through her hair. Dean just stared at her, the dumb smile still plastered on his face.

"Or something," Dean muttered. Ruby rolled her eyes in reply, giving an exasperated sigh. "Someone's bitchy tonight," he continued. Tapping his foot obnoxiously loud on the floor, he watched as Ruby eyed the foot, about ready to pounce. "Easy there kitty."

"You're drunk, aren't you," she deadpanned, her face slouching into what almost seemed to be disappointment.

"So now the Grinch has a heart, huh?" Dean raised an eyebrow.

"_No_, the Grinch just doesn't want to talk to a guy who's completely wasted. Where's Sam?" She went onto her tippy toes, trying to spot the younger Winchester amongst the mess of clothes thrown every which direction, and the boulder of Dean in front of her.

"Gone," was his simple reply, and Ruby watched as his body sagged slightly in the doorway. She could see the muscles tense in his forearm, and noticed the undeniable undertone of pain in his emerald eyes.

"_Gone_?" She felt her natural eyes start to overpower her human's hazel ones, and blinked to return them to normal.

"Is there an echo in here?" Dean taunted. "Yes, Ruby, he's gone." He pushed off of the doorframe, allowing Ruby access to the room. "Don't believe me? Take a gander for yourself."

She did trust him. Despite the fact that he was a demon hating, righteous do-gooder, she trusted him. Looking at the man, she wished that he was the one to be chosen by Azazel, rather than Sam. The pent up darkness in Dean was ten times stronger than that in Sam; Ruby could just feel it. It's always the best soldiers who go dark.

"There're only so many places he could hide in there," she replied. "I trust you." The sentence came out awkwardly, but it still felt oddly good to say. Breathing out, she walked past Dean and into the motel room. She couldn't help but inhale in pinewood scent, the aroma of evergreen trees overtaking her senses. It reminded her torturously well of the place she had grown up. Damn Dean.

"Wow, there's a shocker. So what are you doing here, Ruby?" Dean kicked the door closed with his heel, keeping his arms crossed. Ruby still posed as a threat.

"I want to help," she returned simply.

"Even without your dear old Sammy?" Dean hadn't meant for it to sound so painful and envious, but when it came to Sam and emotions, it was never a good combination for Dean.

"Even then. I'm not like the others, Dean. I want you guys to win; I don't want you to go to hell. I wish I could just be an inhuman demon, but it's not in me. I have a weak spot for humans, and nostalgia I guess."

"It was a 'weak spot' of the Crossroads Demon that got me a one-way ticket to hell."

"No, she just asked you if you wanted to collect two-hundred dollars before passing go; and you said yes." Ruby hated defending other demons, but there it was.

"You just brought Monopoly into this conversation," Dean muttered to himself. "Look, if you _really _want to help, you're gonna have to play by my rules."

"Fine," Ruby replied with a shrug. Dean looked to her quizzically, not able to fully believe the demon.

"Fine… I get to drive."

"Done."

"I pick the motel."

"Deal."

"I get to play the music."

"No." Ruby smirked.

"No?" Dean asked, squinting his eyes slightly.

"Is there an echo in here?" She mimicked Dean from earlier.

"Damn it Ruby, there's no way in hell you're picking the music." Dean shook his head sternly.

"If I'm coming, I get to pick it." She placed a hand on her hip.

"I never asked you to come."

"You need all the help you can get."

"I'll manage."

"You could use the extra body."

"Yeah, maybe, but I'd prefer a body that doesn't want to be the Music Nazi."

"Well, in the words of the Rolling Stones, you can't always get what you want." Ruby supplied Dean with a taunting grin.

"I don't want any Emo crap, got it?" He raised an eyebrow. Was he really allowing Ruby to pick the music? Let alone come with him at all? Losing Sam truly did mess with his mojo…

"I'm a demon Dean, not gothic."

"No Spice Girls either. British bands are overrated…"

* * *

><p>So as always, I have no idea where I'm going with this. Ideas and suggestions would be amazing. I'm also really sorry if some of the characters are OOC. Sam is supposed to be, since he went totally darkside; just FYI.<p>

_Be good and review_


	2. Your Sick, Twisted Smile

_Evil Never Loved You _

_Two _

'_Your Sick, Twisted Smile' _

The open and free road was like Hell. Cold, ruthless, unforgiving, dark. The only colors to be seen were the broken yellow lines of the road, and the occasional passing car with its headlights revealing the blue or red of its body. Was it such a crime to have a classic black or white? Apparently so. Dean blinked, to keep his heavy eyes from closing. He had always loved an empty road to speed across, with no one to hold him back or keep him from living life to the fullest. But what good was a throw caution to the wind type of life, if the freedom he once loved, now felt like his greatest enemy? The thought was anything but warm in the pit of Dean's stomach, and he tried to shake the feeling. He'd mastered long ago how to hold his darkest emotions deep within him, but without Sam around, who was there to hide his true feelings from? Ruby; but she was more of an able body tagging along for a ride she wasn't even invited to.

Taking a hand from the wheel, Dean rubbed his face, to awaken his tired features for the umpteenth time. They were only in Ohio, with almost eight hours left to drive until they reached Virginia. There was no Metallica blasting to keep Dean from falling asleep, and no Sam to argue about what was moral about their job, and what wasn't. Up until now, Dean had always hated when Sammy decided to get all righteous on him, and question the very meaning of their lives, but now it was the only conversation he wished to have.

He wondered where his brother was, and if he was safe. Was he protected somewhere in a relatively warm motel, sleeping away the troubles sure to be plaguing him? Dean hoped so. He didn't even want to imagine the other scenario and fate of Sammy, and rather decided to let his imagination rest.

Leave it to Dean to worry about the very brother he had let slip right from his grasp. What could he say; that was just his style. In the moment, Dean was never the most logical of men. He shot first, and asked questions later. Those questions were ones he usually posed to himself, and they always ended up drowning him even deeper into the darkness he had tried running from for years. Now even Sam, his only little sliver of light, had morphed into the very blackness he despised. But that was life; his cursed, bleak, and painful life. He sighed deeply, shoving the thoughts back into their rusted and aged cage, keeping his eyes sternly on the road in front of him.

"Do you miss him?" Ruby asked nonchalantly from the seat next to Dean. He didn't even turn to face her rough yet endearing features. The darkness of the road held more appeal for him.

"Who," he returned in bleak numbness, wanting nothing but to drown the seriousness with a great Kansas or Styx tune. Alas, Ruby was guarding the tapes in the glove compartment with her life.

"Santa Claus," Ruby drawled in reply, rolling her eyes. Dean could be such a hardheaded Neanderthal when he wanted to be; which was most of the time, usually. Pushing her bangs back with her middle three fingers, she felt her nails scrape against her forehead. Damn, she needed a nail clipper…

"It depends," Dean said with little enthusiasm, gripping the wheel tighter. He was never rough with his baby Impala, but tonight, it didn't seem to matter to him. She wouldn't feel how unyieldingly rough he held onto her wheel, or how heavy his foot slammed on her pedal. His heart dropped. Not even the Chevy '67 could lull his violent pain.

"_Sam_, Dean," Ruby said tightly. "Do you miss _Sam_?" She looked intently at the man beside her, and couldn't help but frown. He was broken. It certainly wasn't hard to notice. She knew why, and to some extent, she understood. But Dean was dangerously like her. Emotions were very insidious friends, when it came to sheer survival. It was those wretched feelings that had gotten Ruby killed in the first place.

"Honestly?" Dean said in a husky whisper, as if he was about to spill his entire life story, "it's none of your business." Ruby was stunned at how easily he could go from a feeble victim, to the very coarseness she had experienced in Hell.

"Oh come on, Dean. This is not the time to be a stony soldier. We have a _long _time until we reach Virginia. We have to pass the time somehow." Her voice was calmer than she had expected it to be. Ruby hadn't used a mild tone with someone, since—since she was human. What wicked power did Dean hold over her?

"We could be passing the time with some _ACDC_, but someone decided that that was too… what word did you use? Right. 'Obsolete'." Dean was very bitter about the whole ordeal, as if Ruby had told him his entire being and life was a superseded mess, just expressed through the music of the rock and roll decades.

"Sorry, I just never got into the good 'ol rock and roll, I guess. Can you blame me? It's so '60s and '70s." Ruby loved nothing more than to pull Dean's strings. He was so invested in his whole ambiance; to change one little detail was akin to the Apocalypse.

"Coming from the demon that's how many centuries old?" Dean raised an eyebrow, finally facing Ruby. He noticed the smirk dancing across her face, and almost let it fool him into thinking this was a happy situation. But he could not deny the uneasiness he felt about someone other than Sammy sitting in that beloved passenger seat. Dean wondered if he'd ever get another chance to see Sam in it again, laughing, and reluctantly singing to all of his music. It all seemed to be a long since lost dream; like the end of an era, the end of a benevolent empire he once loved. He played his role well, though, and supplied Ruby with one of his signature smirks, but it certainly wasn't genuine. The cockiness wasn't hidden in his dimples, and the playful confidence was nowhere to be found in his grassy green eyes.

"Shut up," Ruby returned tightly, crossing her arms. Dean knew he had her pinned. The demon only ever crossed her arms when she was self-conscious or subliminally protecting herself from… ridicule, possibly? Dean hadn't quite yet pinpointed what exactly Ruby was afraid of losing, but he'd find it soon enough.

"Run the case by me again," Dean told her. It wasn't a command necessarily, but it certainly wasn't a mild suggestion either. The tone radiating from his luxurious lips, gave Ruby the vibe she had no other choice but to comply. She somehow didn't mind it though. She _hated _having orders barked at her, but from Dean, it was almost kinky.

"Uh," she responded, remembering what exactly she had read online, "ten people have gone missing so far from the local cemetery, each one found with their neck torn to shreds and a wooden stake in their heart." The news would make any soulful being cringe, but to Ruby and Dean, it was just another day in the neighborhood.

She wondered how Dean could keep an even face, despite how gruesome the situation was. It truly showed just how long Dean has been 'grown up'. Ruby wondered if he ever truly had a childhood. And if so, did he even remember any of it? Even she, a soulless, damned demon, had had a wondrous childhood, of peace and luxury. She almost felt guilty, having those memories when Dean probably didn't even know the meaning of genuine, benign happiness.

"Jesus," he muttered venomously, "I hate vampires." Shaking his head, he ran his right hand through his sandy golden hair, keeping his left palm on the Impala's wheel with a very strong pressure. Moving his medallion back and forth with his thumb and middle finger, he stared absentmindedly ahead of him, not truly seeing anything.

Ruby eyed the necklace. It stood out against his black cloaked body, allowing the faded gold color to shine brightly. The necklace seemed to be his go-to thing whenever he was caught in a situation or state of mind he didn't find agreeable. It was adorably melancholy, and Ruby was eased to know that Dean didn't show these weaknesses around his enemies. They'd have so much to torture him with, and Ruby wasn't sure she'd be able to bear watching it. Dean's entire world was based on fading memories and blind faith. He was a child, caught in the muddy world of adults, and she wasn't sure how much longer he could sustain.

"They're not that bad," she finally returned, her voice much smaller than her usual. "They _were_ human at one point." Ruby shrugged her shoulders.

"Key phrase there, being 'at one point'," Dean returned. She didn't supply him with an answer, so he breathed in, continuing. "Tell me something: why did you want to be here? I didn't take you for the fighting evil type. Shouldn't that be like cannibalism or something?"

"I don't _eat_ other demons, Dean," Ruby shot back dryly. "Besides; evil isn't determined by species. If it was, don't you think all humans would be considered it?" She raised an eyebrow at her stunning driving mate.

"Well geez, Ruby, thanks for not making the conversation bleak or anything…" Dean sped up slightly, as a kind of repellant against this now tense situation.

"Not all demons are bad," Ruby continued, "I mean; if we were, I'd have killed you by now."

"Is that supposed to be a _pleasant _thought?" Dean said, morphing his usual smirk into a certain tone in his voice.

"If that's how you want to take it, then yeah. All I'm saying, is that maybe you're too closed minded about what's good and evil." Ruby again shrugged her shoulders, beginning to fiddle with her nails. Why did Dean Winchester, a simple human man, make her so flustered? If Lucifer could see her now… oh, how dark her punishment would be.

"Enlighten me here then, Dr. Phil." Dean shot her a sideways glance. Maybe she was right; but that didn't mean he was going to lie down and take it.

"You really don't get it, do you?" Ruby shook her head in disbelief. "There is _so _much more that is gray out there, then black and white. You kill these 'evil' things, I get that. But are you sure what you're killing is all bad?"

"I think murdering people constitutes as evil, don't you?" Dean was so not in the mood for this conversation right now. Ruby didn't understand why he was the way he was, and he wasn't about to tell her now.

"You kill," Ruby supplied matter-of-factly.

"So do you, chica. And you're playing this whole 'I'm not evil' card, so don't you think questioning what's a good and bad killing is a little hypocritical?"

"Even if I am being hypocritical, I just don't get it. You claim to know so much about the difference between dark and light, yet you can't even figure it out within yourself."

"Look Philosopher Extraordinaire, you are nine levels of messed up. You threw yourself into my and Sam's life, because he's Azazel's little bitch, but he's not here now; so why are _you_?"

"Sue me, Dean, for caring. I want to help, because I do, alright?"

"You're hiding something," Dean shot back darkly. His green eyes turned to an ominously bleak gray, as he eyed down Ruby.

"So are you there, Winchester. I'm not telling you anything, until you do. Fair enough?" Ruby kept her features stern, not allowing them to waver at Dean's stunningly innocent face.

"Fair enough," he bit out in response.

* * *

><p>Sam stood in the motel room, with little brightness flowing through his body. Dean had killed the one demon that knew all about his powers, so now he was forced to go to the second best thing. It wasn't that he blamed Dean for killing the yellow eyed bastard, it just made for a very long process that he didn't really want to do. Dean could be such an inconvenience. He used Sam as his scapegoat for all the fear he had for himself. HIs "job" was to keep Sam safe from all the evil in the world, when he was the true one to live in fear of it. Sam embraced it, and all that it implied, without a single blink of the eye.<p>

Looking down to the ancient book of dark magic, he read the Latin as if he was part of a human sacrifice ritual, ready to have the gods take the victim away from his sight, ready to bathe in the rewards of the offering. He closed his eyes as he spoke, the words coming from his mouth more akin to his own personal bible than a dark magic he should not be playing with. Feeling the earth beneath him begin to shake violently, he smirked, feeling the dark energy surge through him. Too long he had let the blitheness reign within him.

The shaking soon stopped, the once flickering lights now returning to normal. Opening his eyes, he saw the wondrous Mephistopheles standing before him, crimson red eyes, radiating in the dim lighting…

* * *

><p>Chapter two, yay! So I'm addicted to Supernatural; confession of the day. Thanks to those who reviewed on chapter one, but hopefully more has happened now, to spark those of you who didn't, to drop me a quick note. Haha, just a thought ;) Please tell me any ideas you may have.<p>

_Be good and review _


	3. You're My Favorite Sin

_Evil Never Loved You_

_Three _

'_You're My Favorite Sin'_

Silence.

That was the only sound to be heard in the black Impala as it sped down Route 522. The '67 Chevy hadn't spent many of its years in Pennsylvania territory, but when it did, Dean could always expect at least two or three nicks in the tires from the potholes that littered the roads.

He hated things that targeted his poor baby; especially her wheels. And Pennsylvania was certainly a determined bitch, when it came to roughing up his sweet little 396 Turbo-Jet powered angel. They were somewhere near Lewistown, PA now, cruising on some obscure back road, with little to no scenery available for distraction. Evergreen trees stood hovering along the road, and a few old (and probably haunted) farmhouses littered the rolling hills. A phone-line could be visible from in-between the trees now and again, but that was about it for old Lewie and its surrounding areas.

If Dean had the choice, he'd much rather snap his fingers and be at his destination instead of making the long trip. Now, if Sam was still with him, maybe that wouldn't be the case. There was something so mystically religious about speeding down a long since forgotten road, jamming to the golden years of rock, surrounded by the Impala and Sammy. But now, Dean was no more than an atheist, cynical and jaded about anything that could even breathe a small stench of religion. He wished he wasn't, but it was very rare that his hopes were ever listened to, let alone granted. He'd accepted that long ago, but it still didn't make him any less bitter about the whole thing.

Tapping a stiff index finger on the wheel, he was determined to keep the backbeat of _Eye of the Tiger _stuck in his head. If he concentrated his energy and thoughts on keeping the song in tune and accurate, then maybe his head would shut up about Sam and what used to be… maybe. _Survivor _had never been Dean's favorite band, but their name was uncannily fitting for him. Despite how dead he was inside, his heart was indeed still beating, warm thick blood still making its way through his veins. For all intensive purposes, Dean was still alive; even if just in anatomical terms. Oh, what a joy.

He tried not to let the look of melancholy disgust cross his face.

"You've made your point, Dean," Ruby commented softly from the passenger seat. She'd watched for an agonizing hour and a half as the Winchester silently tortured himself in that over-stimulated head of his.

"What point," he drawled flatly, tightening his grip slightly on the wheel. His urge to flip on the radio was growing stronger.

"I get that you have your secrets," she continued, "and I also get that you don't want to tell me them. That's fine—I'd rather keep my past in the past too." She shrugged, "but we have to talk; do _something_. This car ride is too long and boring to just sit here."

"Any bright suggestions, Switzerland?" _Eye of the Tiger, Eye of the Tiger, Eye of the Tiger_. Dean wouldn't let nostalgia taint him—especially not in front of Ruby. He did have a reputation he had to uphold…

"Yeah, here's one: you let me drive while you sleep, so maybe you won't be such a bitch in the morning." She smiled in sweet coyness, crossing her arms. Although her first and foremost intention was to irk Dean to no end and spark a little fire in him, the guy did seem treacherously tired. Ruby knew he'd probably gone most of his life without a good night's sleep, but this was still no time for him to be a strong martyr. They were getting so close to Virginia; Dean couldn't mess that up now by being overly tired.

"You? This car? Never gonna happen." And that was just the bottom line. No one drove the Impala except for him… and the occasional Sam, and when he was alive, their father. But that was _it_. Baby didn't take well to strangers—Dean had raised her well. She was a Winchester by every slanted and twisted definition. And Winchesters didn't submit willingly and without a fight.

"Why not? I _do _know how to drive." Ruby still found it unfathomable how much a man could love a dingy little piece of metal barely hanging on in the second century it's seen. A certain flare in Dean's eye though, told her that death would be on her horizon if she didn't respect the car.

"There's a big difference between driving, and driving the Impala, sweetheart."

"Woah, it's a stick shift; how so out of this world! You're right Dean, a person could _never _drive this car," she shot back, the sarcasm oozing from her parched but somehow still crimson lips. It reminded her how long it had been since they had had a substantial meal and drink.

"Ten points from Slytherine," Dean returned, equally as sardonic. Ruby could pound him with as many insults, questions, and disappointing looks as she wanted. But the second she stepped into the realm of Sammy and the Impala, Dean would make sure to smite her himself. Damn God; he was too easy on the demons anyway.

"Fine Weasley, have it your way. At least pull over soon—I'm starving."

"What, don't they have French fries in Hell?" Dean taunted, laughing inwardly at his own wittiness.

"Not the kind made of potatoes," Ruby commented matter-of-factly in reply. Dean simply stared at the demon, not about to tempt her to go into any greater detail.

"So I take it there's no salt either," Dean asked passively. He could deal with blood—fine. He could put up with pain—been there, done that. But food and torture were two things he could never associate with one another without feeling sick to his stomach. Not from the repulsiveness, but from the way such a genuinely pleasurable thing such as food would be tainted by all the blood.

"No, no salt." Somehow, that was a very loaded answer and they both knew it. If even just for peace of mind, salt was the go-to repellant for warding off the supernatural. When Dean finally reached his fate of Hell, there'd be nothing to stop him from going under: no salt, no hope, no Sammy, no nothing. It was a terrifying thought to say the least.

Dean only gave a passive nod in return, reaching his right hand to the glove compartment, and pulling out the first cassette tape he could find. Oddly enough, Ruby let him do it. Despite the slightly peeved look on her face, she made no retaliation against his tunes. She was being a good little padawan… demon… padawan-demon thing. Dean smirked, inserting the tape. There was a slight little crackle in the speakers, then nothing but the melodious sounds of _Boston _radiating throughout the car.

* * *

><p>"<em>Hey Dean," Sam said lightly as he flipped absentmindedly through the pages of their father's journal. He watched as Dean lifted his green eyes, still seeming to be focused on whatever article he was reading on the laptop. It wasn't like Dean to choose the laptop and research over the journal and the action, but Sam wasn't about to comment on it. <em>

"_Yeah Sam," his brother finally replied. He seemed so distant, off in his own little world—and it wasn't in the Busty Asian Beauties kind of way. Sam couldn't even begin to imagine what Dean was going through, with Hell being such a solidified fate. Trapped, terrified, unsure… Hell conjured every unnerving emotion known to man. _

"_Do you ever wonder what would've happened if I had let Azazel take me?" The words flowed much easier from Sam's lips than he'd expected them to. He couldn't quite decide if that was a good or bad thing though. That always seemed to be Sam's dilemma. _

"_What the hell kind of question is that?" Dean's words were bitter and sharp. He knew Sam had always been a thinker, fascinated by the numerous outcomes to a scenario, but this took it too far. As of late though, everything seemed to go too far with Dean; and he was usually the one to push the limits. _

"_Just making conversation," Sam replied, regretting even breathing a sound to his brother on the matter. _

"_Well then you must _really _suck in social situations," Dean returned in short sarcasm. _

"_Look, if I'd let Azazel turn me into whatever he wanted me for, then you wouldn't be going to Hell, and maybe even Ash would still be alive. I don't know, I just feel like I've hurt more people trying to run from all of this, then if I'd just accepted it." Sam sunk lower in his chair as Dean glared daggers into his forehead from the other side of the table. The older Winchester whipped the laptop lid closed, making sure it made a good smacking sound as it clicked. _

"_No, you wouldn't have saved anyone if you joined Yellow Eyes. The thing killed Mom, Sam; and Dad, and Jess. I don't think he would've let you have your world peace, with everyone holding hands and singing Kumbaya." Dean's words were dark. There was no mercy, no understanding. If there was one thing he could look at in black and white, it was Yellow Eyes and all the pain he'd caused. Dean was not about to let Sam jumble it all up in a gray heap of 'what ifs'. _

"_I'm serious, Dean," Sam responded tightly, "maybe it would've been smarter for me just to go with him." _

"_Shut up," Dean whispered breathlessly, shaking his head in utter disapproval. "Joining the bastard was never an option, Sam, so why the hell are you bringing it up now?" He rubbed a chilled hand over his face, and then guided it back and forth across his hair. _

"_You're hurting, Dean, you're scared," Sam said innocently. There was no way he could be innocent about this matter though, and Dean knew that all too well; he stood his ground. _

"_I'm not scared," he bit back in reply, moving the computer to his side and placing his elbows sharply on the table. _

"_And here we have the lie of the century, ladies and gentlemen," Sammy drawled. He began to tap his fingers furiously on the table, his nails making incessant noise against the wooden surface. Dean glared at the hand, about ready to stab his knife into the center of it. If there was one thing he couldn't stand, it was nervous tapping. _

"_And what did you think was gonna happen, Sammy? That after you joined him I'd just lay down and die? You know me better than that." Dean was unfaltering on his stance and Sam knew he could do nothing to sway him—no matter how hard he tried. _

"_I don't know what would've happened, Dean, okay? It's just that—if it wasn't for me, you…" _

"_What," he drawled, "have so much more life to live? I'll be dead before I'm forty anyways. So in a way, you did me a favor." _

"_You didn't have to save me," Sam feebly answered. It was twisted, his brother's whole outlook on all of this…_

"_Don't give me that crap; of course I had to save you. How many more people could I meet that can name all of Hawthorne's books, but not name one porno site?" A sad smirk flashed across Dean's face._

* * *

><p>Dean had gone years without his brother. Why was this time so much more painful?<p>

_It was painful every time_, he thought to himself. And it was true.

He was never good without his brother. No matter how much he pretended to be, Dean Winchester was barely able to function without Sam—let alone live. It wasn't that he couldn't; he could adjust to virtually every situation. But there was something about Sammy that made Dean want to leave it all: the job, the pain, the craziness they called a life… his brother made it all bearable. All of the glitches and holes sprung into full gear though, when Sam wasn't around. No one could fill the gap; no Ruby, not John, not Mary, not even Dean's own determination.

Pitiful weakness, warming love.

Damn was it all too crazy.

"Driver Boy," Ruby finally said, "I saw a sign for a diner a mile or so away. So are you done brooding?"

"I wasn't brooding—concentrating," Dean corrected blithely, flipping on his turn signal to get off at the exit.

"Somehow Dean Winchester and concentrating don't really go together in the same sentence," she joked in reply, relieved that she could finally get some decent food in her stomach.

* * *

><p>So awkward place to stop; my bad. I'm totally obsessed with SPN, so I'm sorry if it takes a while to actually introduce TVD into the story. I promise I will though! Haha, ideas and suggestions would be much appreciated.<p>

_Be good and review_


	4. He's Pretty Fly

_Evil Never Loved You_

_Four _

'_He's Pretty Fly' _

The rickety shack of a diner was anything but appealing. Ruby must've been utterly desperate for food, to ever want to go into the place. Dean never really minded a grungy and rundown setting, as long as it had food, and served past one in the morning. This place, Marla's Diner, had both. So in his mind, it should be perfect.

Besides the horridly chipped red paint of the roof, and the dirtied white walls that appeared gray, the diner had real character. It was warm and fuzzy in a way Dean couldn't quite explain. All he knew was that it certainly was very hospitable to any and all kinds of insects, and seemed to welcome the grime that accumulated on the menus. It was simply _charming._

"Great snag here, Ruby," Dean muttered as they sat in one of the booths, "this place is a real five star delight." His mouth was a straight line, obviously signifying the great distaste he had for Marla's Diner. It was odd to him. Usually something like this was no problem; it was amusing, even. But that was when Sam was the one complaining about how the diner they were at violated numerous health laws. Now, there was no reason to treat Marla's as if it was anything better than what it was.

"Oh shut up. It's food, isn't it?" Ruby set her menu on the table, crossing her arms, a kind of tense vibe creeping onto her face. Dean couldn't help but think it was all too contradictory. Ruby claimed to be some sort of impenetrable wall of confidence, yet she was a defensive mess every time he called her out on making a choice or comment that may not have been… the best of options. Maybe dear little demon had a bit of a self conscious streak in her.

"Ask me that in about an hour," he replied dryly as the waitress made her way to the table. Not even the women here could make up for the awful condition of their workplace. She was a very wide woman, with very little coloring in her skin, other than the overly red blush she must've pounded on in the tons that morning. The crumbly mascara was probably bought at a nearby drug store, and her tight off-red curls certainly had to be a perm. Dean wasn't any expert on what women wore and where they bought their stuff, but in the poor waitress' case, even a butch guy like him could see the tragedy of the situation.

"Hi ya'll, what can I get for you?" The lady whipped a pen out of her apron, along with a notepad. A look of determination spread across her face. Yes, her job was very important. And Dean wasn't even being sarcastic about it. This woman held the very delicate task of keeping him fueled for the four hours he and Ruby had left until they reached Virginia.

"Bacon cheeseburger," was his automatic reply, and the waitress gave him a bright smile, her pink lipstick becoming ever so more apparent. Oh Jesus…

Ruby shot Dean a look, displaying a question along the lines of _'what the hell?_ '. Dean just gave her a confused shrug. Turning to the waitress, she smiled. "I'll have the veggie burger, please." She handed the menu to the woman. "Oh, and a side of fries."

The lady gave a nod, and turned to Dean, and he quickly handed her the menu. He wasn't about to get some kind of disease from it. Looking to the nametag pinned on her shirt; he gave her a tight smile. "Thanks, uh, Shirley."

Shirley supplied him with a very happy nod, and then walked away from the table, and through the doors that led to the kitchen.

Dean turned his attention to Ruby. "What are you, a goat or something?"

"Wha—a goat?" She eyed him quizzically, unsure of what exactly Dean was getting at. She placed an elbow softly on the table. Whatever his response was, was sure to be interesting.

"Yeah," he replied. "A veggie burger is very goat-like." He gave a tauntingly disappointed shake of the head.

"What, you have a problem with goats or something? Do you have goataphobia?" She asked him in mock sympathy, a fake look of a psychologist inching onto her features. If the joke wasn't on him, Dean would've found the whole act pretty amusing.

"I'm not a goataphobe," he said in quick dismissal. Despite the lightheartedness of the conversation, he couldn't help but feel a bit melancholy. If Sam were here, he would've corrected Dean, giving him the scientific name for someone afraid of goats. He'd have to look that one up now.

"Then what," Ruby replied, tiring of the joke already.

"A veggie burger? Really? I would've thought you'd go straight for the red meat. Doesn't it remind you of home sweet home?" Dean supplied her with a smirk. Grabbing onto his left forearm with right hand, he placed them on the table. He found himself beginning to tap, much like Sammy always did… had…

"I'm a vegetarian actually," Ruby said with pride, straightening her form a tad. Dean mildly rolled his eyes.

"A humane demon," he deadpanned. "Huh, that's one I'd never thought I'd hear." In all honesty, it didn't really matter to him if she was a vegetarian, vegan, or carnivore. It just gave him something to do, taunting her about it. It almost allowed him to forget that Sam was still out there, all alone, messing with darkness he should've never been introduced to. _Damn it, Sam._ Even when he wasn't here, he still had a knack for making Dean feel responsible, and in turn guilty.

"You're a real caveman when it comes to accepting others, aren't you?" Ruby tried to fight back a laugh. Despite how much she tried to resist him, Dean was just too alluring for her not to notice.

"What can I say? I'm old school."

"Old school for you is like _The Cosby Show _and_ Golden Girls_; you sure you wanna stick with that description?" Ruby morphed her growing smile into a smirk, and tilted her head to the side to get her bangs out of her eyes.

"Cosby had class," he replied. "He and Swayze are the exceptions to the cheesy plague of the 80s." Dean gave a sturdy nod. Sometimes his pride really got in the way. But it was true, Swayze was a boss.

"If you say so," Ruby returned lightly, turning her attention to the kitchen door. She was _so _ready for food. What was taking so long anyways? She and Dean were practically the only ones in the diner. Returning her gaze back to Dean, she figured she'd distract her hungry stomach by continuing to talk. "So once we get to Mystic Falls, what's the plan?"

He simply stared at her numbly. He'd never been asked that before. When he was young, his father had given the orders, and he had followed them—no questions asked. It wasn't a democracy, living under John Winchester's direction. By the time he and Sam began hunting on their own, it was just habitual practice to go about the case as they did; it had never really been planned out.

But Ruby wasn't a Winchester. She hadn't the slightest idea how to go about a job like this. The feeling Dean had in this moment, was quite akin to a candy cane being thrust into his heart, leaving the whole a rusty mess. He had a chance to control the situation. But it also meant the end of what used to be…

"Uh," he finally choked out, "well, hunting rule number one: identify the creature." It was a weak response, mediocre humor at best—but it was all he could muster. Ruby was entering into a world Dean never let people into. It was hard to accept that freely.

"I thought you said it was a vampire," Ruby returned hesitantly. She didn't think she'd ever truly understand what went on in that head of Dean's, but she was still irked at how jumbled he made her.

"I _think _it's a vampire. We won't know until we see the bodies, and look over the lore." Ugh, this was all too bland. Dean had spent his entire life trying to get his way through looks, charm, and humor, since his father was always the one to call the shots. Now that he was finally given the opportunity to walk in his father's shoes and be the undisputed leader, he didn't really want the role. A few years back he would've jumped at the chance. God, how he had changed.

"_Research_?" She complained, slumping in her seat, and giving a quick glance towards the kitchen; she could hear shuffling. Food had to be on its way. "What happened to the shoot first, think later philosophy of yours?"

Dean stifled a sigh. "With Sam gone, I have to play both roles now." Ouch, it was hard to admit that. As much as he regretted voicing true feelings to Ruby, he didn't really mind. It felt good to say out loud the undeniable truth. He couldn't have run away from it forever, anyways.

"No, _we _have to play both." Ruby was firm on her reply. Dean wouldn't be alone on this. As much as she hated structure and research, she knew he hated it ten times more. If he could go on, altering himself to uphold some form of stability, so could she. They were partners. Whether or not either of them fully accepted that yet, was insignificant. They needed each other.

"Here we go, ya'll," Shirley said in disgusting sweetness as she placed the food on the table. Dean and Ruby gave mummers of a thank you, and then dove right into their food. It was shockingly better than he had imagined it to be. He'd eaten worse; so this was pretty normal. Maybe the lettuce was a little floppy, and the bun could've been a tad fresher, but all in all, it was pretty decent considering.

Ruby though, had a look of nauseating horror on her face. Looking to her veggie burger, she said tightly, "it almost makes me want meat."

Dean couldn't help but chuckle, and took an enormous bite from his own burger. "Your fault for trying to be a goat," he joked.

"You suck, you know that?" She let her burger fall back onto the plate, and she tore into her French fries, devouring them at an overwhelming rate.

"Duly noted, Frenchavore," he replied, shaking his head in amusement before taking another bite of his bacon cheeseburger.

* * *

><p>The car was utterly silent, as per usual with Dean and Ruby, as they continued on their way to Virginia. It was about two in the morning, and Dean was fighting to stay awake.<p>

"Tell me about Sam," Ruby said quietly. She was very curious of the relationship the Winchester brothers had, and figured now was as good a time as any. She knew Sam was on Dean's mind constantly, and it would give him a reason to stay awake. If only to fight about not telling her.

He breathed heavily. "No," he replied meekly. He lifted his eyes to meet hers. That was certainly a first. Maybe she was finally getting somewhere with him.

"Dean, you can't run from him forever. And keeping everything bottled up inside of you won't help either. There's nothing wrong with talking now and again; _really _talking." She eyed him with unfaltering determination. She'd make him face the touchy subject one of these days.

"Fine," he bit out tiredly, too weak to fight with her, "you really wanna know?"

Ruby nodded.

"He's—he's everything someone could ever want. When we were kids, Sammy would always question my dad's motives, and I used to think that he hated that. It took me a long time to realize that dad _respected _it. Loved it, even. Sam was bold in a way I could never be. He wasn't a rebel without a cause. He was so much more methodical about it all. Everything that kid's ever done in his life is for some specific reason. With me, I'm lucky if I can make one up on the spot. I follow orders. Sam never has. And it's weird, because I should be the one questioning the authority; Sam's usually so compliant. But that's where people have him wrong: he's a true rebel if I've ever seen one. Sometimes I wish I was more like him. Maybe then I could finally be the person everyone thought I'd turn out to be, but never could be."

It was miraculous to Ruby, listening to Dean talk like this. He was much more articulate than he let on, and he was in much more turmoil and pain than she'd originally thought him to be. He was far past broken. He seemed to depend on Sam on such a deep level, that losing him, was like losing every part of himself he ever found redeemable.

He was more like Sam than he knew, though. Ruby could see it. It was as blatant as day, but Dean still refused to look. Maybe he didn't rebel quite like Sam had done, but he was indeed still doing it. She'd show him that. One way or another.

* * *

><p>So this chapter really got away from me. So sorry if it's really OOC and cheesy. Haha. I have so many other stories I should be working on, but as I keep saying, I'm addicted to this.<p>

_Reviews are love _


	5. An Enemy Bigger than My Apathy

_Evil Never Loved You_

_Five _

"_An Enemy Bigger than My Apathy" _

Ice. That was all Sam felt. Despite the humid late spring weather, he was surrounded by coldness. If he really was supposed to be a soldier of Hell, he'd have expected to feel fiery; sweating profusely the sinister intensions of the demons down under. But apparently Hell was cold. Well, Sam's own personal Hell on earth was, at least.

Sinking deeper into the chair placed in the corner of the little motel room, he eyed his summoned demon guardedly. The man Mephistopheles possessed was practically the Hulk. A massive height of at least 6'5", even Sammy felt small in comparison. But it wasn't the height that tempted him to run away as fast as his legs would take him. It wasn't the blackened insidious smirk that crept on his face like a million scurrying spiders. It was the eyes. They were kind: emerald green, with an amber ring circling the inner-most part of the iris, and pastel blue swirling subtly and happily around the frontier. Dean's eyes.

Rubbing a hand over his tense face, Sam breathed in deeply, hoping to disperse the feelings of nostalgia. He had chosen to leave Dean. There was no going back. Even if he wanted to, he knew his brother would never welcome him; not truly. The fact filled Sam with hate. There was no reason for him to pretend to be benevolent now. _But you are good_, a voice pleaded softly in his head. It wasn't quite Dean's voice, wasn't exactly his own conscience. Whatever it was, it certainly painted the door to his left in a very tempting light.

"Oh, don't look so longingly towards the door, Sam. It might lead someone to believe you were planning on leaving." Mephistopheles' voice was oily. A natural tone of threat mutilated his words, and his smirk intensified, becoming more of its own horror image than simple smugness. Sammy held back a gulp. _Stupid, stupid, stupid_.

"Wh—What? I would never—"

"Don't play dumb now. If you want to live through this with as little wreckage as possible, you'd best start stifling those lies." His glare was poisonous. Knowing demons, it probably legitimately was. But Sam didn't let the warning stare get to him too strongly. He focused rather, on the little humor that could be salvaged. For a demon, Mephistopheles sure was wordy. If Dean were here with him, he'd probably make some crack joke about how he was a Shakespeare wannabe or something. But all there were was Sam, a demon, and ice.

'Now tell me: did you summon me here just to have me cooling my heels? I was having a_ marvelous _time in Hell."

"I want to join you," Sam returned. The words came out stronger than he'd anticipated them to. A slight sickening feeling crept into his stomach, but he tried his best to ignore it. _You're being an idiot…_

"Join us," Mephistopheles drawled in echo, "is that so."

Sam nodded, and the demon raised a dark eyebrow, obviously not convinced.

"Yeah, it is," Sam replied, edginess finding its way into his voice.

"Don't act so surprised," the demon returned tauntingly, "you have never been the most—complainant, of humans."

"I'm compliant now," Sam said, holding what little ground he had left. _Terrible, terrible idea. _

"Yes, yes, of course you are," Mephistopheles returned sarcastically. "Only until your partner in crime can jump out and get a shot off with that _inconvenient _Colt of yours." The demon crossed his arms, his eyes flickering dangerously. He began to pace ever so gracefully around the room, slowly but surely circling Sam like a vulture.

"It's just me," Sam said simply. And that's when it sunk in. That's when the loneliness became apparent in his chest, and the vacant spot next to him enveloped him in all he was missing; leaving behind.

"Give me one reason why I shouldn't wring your neck right here." It wasn't as sinister a tone as Sam would have expected from a demon like Mephistopheles. Of course, the evil brute force still made a home in the crevices of his words, but Sammy didn't feel trapped by them.

"You need me," Sam replied, the dark cockiness shining through. _Power. _

"No need to flatter yourself now. You're not as irreplaceable as you claim to be." Mephistopheles paused. "But, if you could prove your loyalty…" his eyes flickered greedily, and sadistic urges shined forebodingly on his set of pearly whites. Sam's arms suddenly felt heavy on the armrests of his chair.

"What would you have me do?" _Submission_. It was something he'd never had a knack for. Sam never took well to people telling him what to do. His father, Dean, Bobby, teachers… they all seemed like boulders, keeping him from what he was truly capable of.

"If you truly want to fulfill Azazel's plan for you, then killing… oh, I don't know—your brother for instance, wouldn't be a problem at all. Would it _Sammy_?" Evil son of a bitch. Sam's fingers clenched, digging deeply into his palms. He couldn't. He'd never. It was impossible. Dean was his brother. He was more than that even.

"I—" he choked. Breathing shallow, pulse pounding uncontrollably in his throat, and body paralyzed, Sam lifted his heavy eyes to meet Mephistopheles. What an agonizing image it was.

"Take it or leave it," Mephistopheles replied dismissively. He started edging his way towards the door, and Sam began to panic. He couldn't let a demon like Mephistopheles roam free, and couldn't go running back to what used to be, either. He'd gotten himself caught. _Damn. _

Sam didn't want to. He'd rather die, than have to kill his own brother. But he'd made such a point about taking this path. God that sounded heartless. But he couldn't let emotion get in the way here. If he really was going to do this, Dean would have to become simply a target. A bump in the road. He couldn't be a brother; or a friend; or a companion. Dean Winchester was no one. _But he's everything_.

"I'll—I'll," Sam stopped momentarily, "I'll do it." And that was the stake. Going straight through his heart. The day Sam put greed and power before his own brother, was the day he truly became evil.

{X}

* * *

><p>"Remind me again why I let you drive," Dean muttered from the passenger seat, head still lying against the window, eyes barely registering what they were seeing.<p>

"You needed to sleep, Aurora," Ruby taunted, smirking. She pressed her foot on the pedal a little harder, causing Dean to jerk forward. He glared towards her, but made no comment.

"Who the hell is Aurora?" He questioned. Sleepiness blended with confusion. Dean wasn't in any mood to make a snarky comeback.

"Haven't you ever seen _Sleeping Beauty_?" She raked a hand through her hair. God, did it need washed.

"Sorry sweetheart, never really had time for Disney. I was too busy, you know, shooting guns and all." Lifting his heavy head upright, he shook it a few times to try and wake up his senses.

"Aw, that's too bad. You never got your chance to be a pretty little princess," she drawled.

"See? That right there? It's comments like that that make me _really _want to shoot you."

"You're certainly a bundle of joy in the morning, aren't you?"

"Bundle of joy with a gun," Dean muttered. Eyeing Ruby, he hated the sight he saw. Her bony, demony hands around his sweet baby's wheel. She must be crying right about now. _Don't worry, baby, the mean lady will be out of your hair soon… _

"We've got about another hour until we get to Mystic Falls," Ruby replied softly, easing up on the speed.

"No, no, sweetheart, don't slow down now." He wanted out of this car. It was like the road trip from hell.

Ruby sighed. "Can we take a break for a second? I can't stare at the road for another second." Dean didn't object, so she pulled the Impala off to the side, and eagerly got out of the car. Tapping a hand on the dashboard, Dean also slipped out of the car, happy to stretch his muscles.

Walking past Ruby, until there was a significant distance between them, he pulled his phone out of his jacket pocket. Flipping it open and scrolling through his contacts ever so slowly, he finally made his way to the name "Sam". He stared at the number, wanting nothing more than to press call. He knew he shouldn't do it. Sam would want his space, and Dean was still mad as hell at the idiot. But he was still his brother.

Pushing aside his better judgment, he hit call, and brought the phone up to his ear tensely. It rang, and rang, and rang, and rang. But no answer. Finally, it went to voicemail.

'_Hey, you've reached Sam. I'm not available right now, but leave your message after the beep, and I'll get back to you as soon as possible_'. Such a typical voicemail. Dean sighed. He should hang up. Yet he still lingered.

"Sammy, it's Dean. Call me when you get this." Flipping the phone shut harshly, he put it back in his pocket and made his way over to Ruby.

* * *

><p>Very short chapter. But the next one is going to be filled and long (hopefully, haha), so stay with me here. Lol. Ideas are always appreciated.<p>

_Be good and review _


End file.
